N-(1-adamantyl)-5-(2-heptyloxyphenyl)isoxazole-3-carboxamide | 1450606-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(1-adamantyl)-5-(2-heptyloxyphenyl)isoxazole-3-carboxamide
• 英文别名: N-(1-adamantyl)-5-(2-heptoxyphenyl)-1,2-oxazole-3-carboxamide
• CAS: 1450606-96-8
• 化学式: C₂₇H₃₆N₂O₃
• 分子量: 436.594
• InChiKey: WVJKYUFVJFXBIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-heptyloxyphenyl)ethanone 在 盐酸羟胺 、 sodium ethanolate 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 52.75h， 生成 N-(1-adamantyl)-5-(2-heptyloxyphenyl)isoxazole-3-carboxamide
  参考文献：
  名称：

  3-Carboxamido-5-aryl-isoxazoles as new CB2 agonists for the treatment of colitis

  摘要：

  Recent investigations showed that anandamide, the main endogenous ligand of CB1 and CB2 cannabinoid receptors, possesses analgesic, antidepressant and anti-inflammatory effects. In the perspective to treat inflammatory bowel disease (IBD), our approach was to develop new selective CB2 receptor agonists without psychotropic side effects associated to CB1 receptors. In this purpose, a new series of 3-carboxamido-5-aryl-isoxazoles, never described previously as CB2 receptor agonists, was designed, synthesized and evaluated for their biological activity. The pharmacological results have identified great selective CB2 agonists with in vivo anti-inflammatory activity in a DSS-induced acute colitis mouse model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.010